A 1:1 co-crystal of the herbicide triflusulfuron-methyl and its degradation product triazine amine

Abstract

The herbicide triflusulfuron-methyl (systematic name: methyl 2-{[4-dimethyl­amino-6-(2,2,2-trifluoro­eth­oxy)-1,3,5-triazin-2-yl]carbamoylsulfamo­yl}-3-methyl­benzoate) and its degradation product triazine amine [systematic name: 2-amino-4-dimethyl­amino-6-(2,2,2-trifluoro­eth­oxy)-1,3,5-triazine] form a triclinic 1:1 co-crystal of the title compound, C7H10F3N5O·C17H19F3N6O6S, in which its two components are connected via a pair of complementary N—H⋯N hydrogen bonds, similar to the monoclinic crystal structure of the parent compound triflusulfuron-methyl [Mereiter (2011 ▶). Acta Cryst. E67, o1778–o1779] in which a pair of mol­ecules related by a twofold axis are linked by two N—H⋯N bonds. The triflusulfuron-methyl mol­ecules of both crystal structures are similar in geometric parameters and conformation, which is due to stiffening by a short intra­molecular N—H⋯N bond [N⋯N = 2.620 (4) Å] and an intra­molecular dipole–dipole inter­action between the sulfamide and the carboxyl moieties, with Os⋯Cc = 2.802 (5) Å and Oc⋯Ns = 2.846 (4) Å. Inter­molecular N—H⋯O hydrogen bonds and slipped π–π stacking inter­actions between the diamino­triazine moieties [perpendicular distances of 3.25 Å within hydrogen-bonded tetra­mers and 3.27 Å between adjacent tetra­mers] link the two constituents of the co-crystal into columns parallel to the a axis. An intra­molecular C—H⋯O hydrogen bond occurs in the triflusulfuron-methyl mol­ecule and inter­molecular C—H⋯O inter­actions between triflusulfuron-methyl mol­ecules occur in the crystal structure. In the triflusulfuron-methyl molecule the dihedral angle between the least-squares planes of the two rings is 75.8 (1)°. In the triazine molecule, the CF3 group is partly orientationally disordered.